O,O-Dipyridin-2-yl carbonothioate → 4,7-Dimethyl-5-benzimidazolylisothiocyanate

HRID 1736463Notes

Reaction equation

HRID 1736463 reaction equation
C1C=C(O[C:8](OC2N=CC=CC=2)=[S:9])N=CC=1.[NH2:17][C:18]1[CH:26]=[C:25]([CH3:27])[C:21]2[N:22]=[CH:23][NH:24][C:20]=2[C:19]=1[CH3:28]>CN(C)C1C=CN=CC=1.C(Cl)Cl.CO>[CH3:28][C:19]1[C:20]2[NH:24][CH:23]=[N:22][C:21]=2[C:25]([CH3:27])=[CH:26][C:18]=1[N:17]=[C:8]=[S:9]

Participants

6

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 183798614,7-dimethyl-3H-benzimidazol-5-amine

Product 1

HCID 214727244,7-Dimethyl-5-benzimidazolylisothiocyanate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of di-2-pyridyl thionocarbonate (2.29 g) and 4-dimethylaminopyridine (0.03 g) in CH2Cl2 (150 mL) is added dropwise over 30 minutes a solution of 5-amino-4,7-dimethylbenzimidazole (0.816 g) in methanol (50 mL). The mixture is stirred for 3 hours at room temperature, then rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with a gradient of 50% to 80% ethyl acetate/hexane to afford 4,7-dimethyl-5-benzimidazolylisothiocyanate as a white solid.

Workup

  1. customThe residue is purified by flash chromatography on silica gel
  2. washeluting with a gradient of 50% to 80% ethyl acetate/hexane

Sources & evidence

ORD record
ord-80e7db9e6e82480cb85c6b6cd20d3025
Source dataset
uspto-grants-1996_07
Patent number
US05541210

Reaction notes

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